Originally Posted by wanderingstar0

So the last time I bought a bike was ten years ago and I just went to Canadian Tire (think Wal-Mart) and bought a mountain bike. Well time passed, I got fat and stopped doing anything. Previously to that I road my Grandfathers old ten speed. I enjoyed that bike way more. Made some changes this year, lost 90lbs and started thinking about biking to work. Its about 12KM each way on mostly paved paths and some city streets. Started researching a bike to do just that and was surprised by both the variety and especially price of whats available. I quickly became overwhelmed by choice. So I decided to go to some LBSes and see what they had. I went to three and was given three different suggestions and test rides. I've test ridden a hybrid ($500), road bike ($750) and cyclocross bike ($820) based on their suggestions. Perhaps you get what you pay for but the one that put a smile on my face was of course the cyclocross bike. It felt great to ride, quick and easy to control. It was a Norco Threshold A3. Of course that was a little out of the budget range I originally set out (about $400) but I'm thinking now that is unrealistic. I've started looking used, but I have no idea what to look for.

This is the long way of saying that I'm looking for advice. Here is what I liked about what I tried:

1. Drop Bars - I found the hybrid seating position very uncomfortable, especially in the hands
2. Weight (somewhat) - I need to carry it up two flights of stairs. Both the road and cyclocross bike were nice in this regard.
3. Index shifters - This is where I'm having issues with used, since most are too old to feature this (that I've found so far)
4. Fenders and a rack - I'm going to want to add both of these for my commute. I'll be carrying a laptop and cloths every day.

Am I better off looking used and if so what should I be looking for? Any great deals on a road / cyclocross bikes I may be missing? Is it worth just saving up for a little longer and buying higher end? I know this is super vague but I'm really feeling overwhelmed by choice. Any advice would be appreciated.